I didn't even think about using the app! Is it available for both iPhone and Android? And do I need to create an account first or can I just download it and pay?

Yes, it's available for both iPhone and Android. You download it from your app store for free. You don't need to create an account beforehand. You just download the app, go to the "Payments" section, and it will give you options to pay. You'll need basic info like your SSN/ITIN, date of birth, and filing status to verify your identity. For payment you can choose Direct Pay (bank account) or pay by card through a payment processor (which charges a fee).

Good advice! I also take screenshots of the payment confirmation page. Learned that lesson the hard way after a payment "disappeared" from their system a few years ago.

Screenshots are definitely smart too. I've started saving everything as PDFs now - confirmation pages, notices, everything. The IRS lost my payment and then tried to charge me interest and penalties before they fixed it. Never again!

16 That's a good point about different software. I've actually gotten different results between TurboTax and H&R Block before. Which tax software do you think is most accurate for state returns specifically?

9 I've found that TaxAct and H&R Block are both pretty good for state returns. Each software has its strengths, but the questions they ask can sometimes lead to different deductions being found. As for accuracy, they all use the same tax laws and formulas, so technically they should all give the same result if you enter identical information. The differences usually come from how they guide you through the process and what deductions they help you discover.

11 This happened to me too! I moved from California to Arizona and filed full-year for both states accidentally. Ended up paying double taxes until I figured it out and filed amended returns.

How do you know if you need to make quarterly payments? I started some freelance work this year but have no idea how much I'll make or how to handle the taxes.

Generally, you need to make quarterly estimated payments if you expect to owe $1,000 or more when you file your tax return. This applies to income that doesn't have taxes automatically withheld - like freelance work, rental income, investments, etc. A good rule of thumb is to set aside about 25-30% of your freelance income for taxes (covers both income tax and self-employment tax). You can make quarterly estimated payments through the IRS Direct Pay system or IRS.gov/payments. The due dates are usually April 15, June 15, September 15, and January 15 of the following year.

Yes! This happened to me too! I called my bank beforehand this year to let them know I was going to make a large payment to the IRS. They put a note on my account and everything went smooth. Definitely recommend giving your bank a heads up.

Love this Sims-like approach! Would there be different character "classes" like entrepreneur vs. employee? Each would have different tax situations and strategies. Also would be cool to have seasonal events like tax season, open enrollment for benefits, etc.

Absolutely! Different career "classes" would be a fantastic way to introduce various tax situations. Entrepreneurs would deal with self-employment taxes, quarterly estimated payments, and business deductions. Employees would focus on W-2 optimization, benefit elections, and retirement account choices. Seasonal events would definitely be included! Tax season would be a major yearly milestone, with preparation activities in the months leading up to it. Open enrollment periods would prompt players to make healthcare decisions that impact both their tax situation and financial security. I'd also include annual financial checkpoints where players review their progress and adjust their strategies for the coming year.

An investment competition would be fun, but I think plenty of people would play a tax game if done right! Look at how popular games like Papers Please became - literally about checking documents. If you make the mechanics satisfying and include enough strategy elements, even "boring" subjects can become addictive. Tax optimization is basically a puzzle game anyway!

Does the withholding rate change if your income is higher? I make about $180k and my company withholds 37% on RSUs which seems excessive, but maybe that's correct?

Yes, the withholding rate does change at higher income levels. For supplemental wages (including RSUs) over $1 million, the mandatory withholding rate is 37%. For supplemental wages under $1 million, the employer can choose either a flat 22% rate or aggregate the amount with your regular wages and withhold at your normal income tax rate. If your company is withholding at 37% for all RSU vesting regardless of amount, they're using a conservative approach that will likely result in overwithholding for most employees. This isn't incorrect, just cautious. Some companies do this to ensure employees don't end up with unexpected tax bills. You'll get any excess back when you file your return, or you could adjust your W-4 on your regular paychecks to compensate.

Wow, I didn't even think about the state tax aspect! That could definitely explain part of the difference I'm seeing. I'll have to go back and look more carefully at my vesting statements to see the breakdown of federal vs state withholding. Thanks for pointing this out!

Happy to help! Also check if your company does any FICA (Social Security/Medicare) withholding on the RSUs too. Some companies handle this by withholding extra shares, while others might reduce your next regular paycheck to cover these taxes. That's another reason your "received" amount might be less than what shows up as income on your W2.